CN113603695B - Substituted pyrimidinamine compound or salt thereof acceptable as pesticide, composition and application thereof - Google Patents

Substituted pyrimidinamine compound or salt thereof acceptable as pesticide, composition and application thereof Download PDF

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CN113603695B
CN113603695B CN202110895921.9A CN202110895921A CN113603695B CN 113603695 B CN113603695 B CN 113603695B CN 202110895921 A CN202110895921 A CN 202110895921A CN 113603695 B CN113603695 B CN 113603695B
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halo
alkoxy
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CN113603695A (en
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葛家成
李丽
孙鹏
马娥
胡堂路
刘明东
邢阳阳
杨春河
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Qingdao Hengning Biotechnology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

The invention belongs to the field of pesticides, and particularly relates to a substituted pyrimidinamine compound or a salt and a composition thereof acceptable as pesticides and an application thereof, wherein the compound has a structure shown in a formula (I):

Description

Substituted pyrimidinamine compound or salt thereof acceptable as pesticide, composition and application thereof
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to substituted pyrimidinamine compounds or salts and compositions thereof which are acceptable as pesticides, and application of the compounds or the salts and compositions thereof which are acceptable as pesticides as bactericides.
Background
Compounds having a pyrimidinamine structure are described in patents WO2003049542A, WO2012065574A and are reported to have bactericidal biological activity. WO2012065574A reports that substituted pyrimidinamine compounds capable of controlling harmful bacteria have good activity on cucumber downy mildew, wheat powdery mildew, wheat rust, rice blast and the like. However, the control activity against the control target including cucumber downy mildew and wheat powdery mildew is not satisfactory at a low dosage.
Technical problem
In order to solve the problems in the prior art, the invention provides a substituted pyrimidinamine compound or a salt thereof acceptable as a pesticide, a composition and application thereof. The applicant has unexpectedly found that the substituted pyrimidinamine compounds or the salts thereof which are acceptable as pesticides have excellent biological activity on wheat powdery mildew, excellent control activity on objects such as cucumber downy mildew and excellent safety on crops.
Technical solution
The technical scheme adopted by the invention for realizing the purpose is as follows: a substituted pyrimidinamine compound or a pesticidally acceptable salt thereof, having the formula:
Figure BDA0003197889090000011
in the formula (I), the compound is shown in the specification,
R1selected from H, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6Alkoxy, n is an integer selected from 0 to 5;
R2is selected from H or C1-C6An alkyl group;
R3selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or C3-C6A cycloalkyl group;
R4selected from hydrogen, halogen, C1-C8Alkyl, halo C1-C8Alkyl radical, C1-C8Alkoxy or C3-C8A cycloalkyl group;
R5selected from H, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
R6selected from H, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
or, R5And R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 8;
R7selected from H, halogen, CN, nitryl, aldehyde group, carboxyl, hydroxyl and C1-C6Alkyl, halo C1-C6Alkyl radical, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl, unsubstituted aryl or substituted aryl.
Further, in the formula (I), R1Selected from H, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4Alkoxy, n is an integer selected from 0 to 5;
R2is selected from H or C1-C4An alkyl group;
R3selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or C3-C6A cycloalkyl group;
R4selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or C3-C6A cycloalkyl group;
R5selected from H, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R6selected from H, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
or, R5And R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 7;
R7selected from H, halogen, CN, nitryl, aldehyde group, carboxyl, hydroxyl and C1-C4Alkyl, halo C1-C4Alkyl radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl, unsubstituted phenyl or substituted by C1-C4Alkyl-substituted phenyl.
Further, in the formula (I), R5And R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 6.
Further, in the formula (I), R1、R2Each independently selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt, CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3、CH2CF3、CH2CH2Cl, vinyl or cyclopropyl;
R3、R4each independently selected from H, F, Cl, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt or cyclopropane;
R5and R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 5;
R7selected from H, F, Cl, Br, CN, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3、CH2CF3、CH2CH2Cl, vinyl, OMe, OEt, n-PrO, i-PrO, n-BuO, i-BuO, s-BuO, t-BuO, cyclopropane, nitro, aldehyde group, carboxyl and hydroxyl.
Further, in the formula (I), R1、R2Each independently selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt or cyclopropane;
R3、R4each independently selected from H, F, Cl, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt or cyclopropane;
R5and R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 5;
R7selected from H, F, Cl, Br, CN, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3Vinyl, OMe, OEt, n-PrO, i-PrO, n-BuO, i-BuO, s-BuO, t-BuO, cyclopropane, nitro, aldehyde group, carboxyl group and hydroxyl group.
Further, in the formula (I), R1、R2Are all H, and n is 5;
R3selected from H, Me or Et;
R4is n-Bu;
R5and R6Together form a radical- (CH)2)t-, t represents 3 or 4;
R7selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, cyclopropane.
Further, it is selected from:
Figure BDA0003197889090000031
the agrochemically acceptable salt can be a salt prepared by reacting the substituted pyrimidinamine compound with a chemically acceptable acid, wherein the chemically acceptable acid can be an inorganic acid (such as hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid) or an organic acid (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzoic acid); the pesticide acceptable salt can also be a salt prepared by reacting the substituted pyrimidinamine compound with a chemically acceptable base, wherein the chemically acceptable base can be an inorganic base (such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate) or an organic base (such as trimethylamine, triethylamine and the like).
Further, the pesticidally acceptable salt may be a potassium, sodium, ammonium, calcium, pyridinium or choline salt.
The invention also discloses a sterilization composition, which comprises at least one of the substituted pyrimidinamine compounds or the salts thereof acceptable as pesticides, wherein the substituted pyrimidinamine compounds comprise an effective sterilization amount; further, the preparation also comprises a preparation carrier or a preparation auxiliary agent.
The invention also discloses a method for controlling plant diseases, which comprises applying a biologically effective amount of at least one of the substituted pyrimidinamine compounds or their salts acceptable as pesticides or the bactericidal composition as described above on plants.
The invention also discloses the application of the substituted pyrimidinamine compound or at least one of the salts thereof which can be accepted by pesticides or the bactericidal composition in the aspect of controlling plant diseases; preferably, the plant disease is a viral disease, a bacterial disease or a fungal disease.
In the definitions of the structural formulae of the compounds mentioned above, the terms used have the following meanings:
halogen or halogen: refers to fluorine, chlorine, bromine, iodine.
C1-C6Alkyl groups: straight or branched chain alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or tert-butyl.
Halogen substituted C1-C6Alkyl groups: straight or branched alkyl groups having 1 to 6 carbon atoms in which some or all of the hydrogen atoms are replacedHalogen, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.
C2-C6Alkenyl: a linear or branched alkenyl group having 2 to 6 carbon atoms, such as an ethenyl group, a propenyl group and the like.
Halogen substituted C2-C6Alkenyl: a straight chain or branched alkenyl group having 2 to 6 carbon atoms, in which hydrogen atoms may be partially or entirely substituted with halogen, for example, a chloroethenyl group, etc.
C1-C6Alkoxy groups: a linear or branched alkyl group having 1 to 6 carbon atoms bonded to the structure via an oxygen atom bond.
halo-C1-C6 alkoxy: straight or branched alkoxy having 1 to 6 carbon atoms, wherein hydrogen atoms in the alkoxy groups may be partially or wholly replaced by halogen, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.
The radical abbreviations appearing in the present invention are in accordance with those commonly used in the art, e.g., Me represents methyl, Et represents ethyl, Pr represents propyl, Bu represents butyl, n-Bu represents n-butyl, i-Bu represents isobutyl, s-Bu represents sec-butyl, t-Bu represents tert-butyl, phenyl represents phenyl, OMe represents methoxy, etc.
A method for synthesizing a compound represented by the formula I comprises the step of reacting a compound represented by the formula III with a compound represented by the formula II (in the chemical formula shown below, the substituents and symbols have the same meanings as those defined in the formula I as long as the substituents and symbols are not defined in any other way) in the presence or absence of an alkaline reagent and in the presence or absence of a solvent to obtain a target compound represented by the formula I. The compounds represented by formulae II, III are commercially available or can be prepared by methods described in EP 407192A:
Figure BDA0003197889090000041
further, the solvent is one or more selected from acetonitrile, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dichloromethane, benzene, toluene, xylene, dichloroethane, and ethyl acetate;
further, the reaction may be carried out under normal pressure or high pressure, preferably under atmospheric pressure, and the post-treatment may be carried out according to a conventional method.
The compounds of the formula I according to the invention or their salts, respectively compositions, which are acceptable as pesticides are suitable with outstanding efficacy as fungicides, in particular as fungicides or bactericides, some of which are systemically effective and can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Furthermore, they are suitable for controlling harmful fungi, which occur in particular in wood or in the roots of plants, in particular for treating fungi or bacteria, or materials, plants, soils or seeds to be protected against fungal or bacterial attack, with an effective amount of at least one compound of the formula I as defined according to the invention or as a pesticidally acceptable salt, composition. Especially suitable for food crops, such as the gramineous food crops.
The compounds I according to the invention or their salts and compositions as pesticides are suitable for use in various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; sugar beets, such as sugar or fodder beets; fruits such as pomes, stone fruits or berries, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries or blueberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palm, peanuts or soybeans; cucurbits, such as squash, cucumber or melon; fibrous plants, such as cotton, flax or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, cucurbits or bell peppers; laurel plants, such as avocado, cinnamon or camphor; crops of greater economic value, such as corn, soybean, oilseed rape, sugar cane, oil palm, tobacco, nuts, coffee, tea, bananas, grapes, hops, and the like; lawn; natural rubber plants or ornamental and forest plants, for example flowers, shrubs, broad-leaved trees or evergreens, for example conifers, and plant propagation material, for example seeds, tubers, cuttings and the like, for controlling plant diseases, in particular fungal diseases or bacterial diseases.
Preferably, the compounds I or their salts, compositions, respectively, are used in field crops, for example potatoes, sugar beet, tobacco, wheat, rye, barley, oats, rice, maize, cotton, soybeans, oilseed rape, leguminous plants, sunflowers, coffee or sugar cane; fruits; preventing and treating fungal or bacterial diseases on ornamental plants or vegetables such as cucumber, tomato, kidney bean or pumpkin.
The invention also provides a bactericide composition comprising a compound of formula I. The compounds of formula I can be formulated in a variety of ways depending on the general biological and/or chemical and/or physical parameters. Examples of suitable formulation choices are: wettable Powders (WP), wettable liquids (SL), Soluble Powders (SP), dispersible liquids (DC), Aqueous Solutions (AS), Microemulsions (ME), Emulsifiable Concentrates (EC), aqueous Emulsions (EW), sprayable solutions, Suspensions (SC), dispersible oil suspensions (OD), powders (DP), microcapsule suspensions (CS), water dispersible granules (WG), water Soluble Granules (SG), macrogranules (GG), granules for spreading and soil application (GR), Aerosols (AE), ultra low volume agents (ULV) and wax products. Necessary formulation auxiliaries, such as inert substances, surfactants, solvents and other additives.
Examples of suitable additives are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, anti-freezing agents, anti-foaming agents, colorants, tackifiers, and binders.
Suitable solvents and liquid carriers are water and/or organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, such as toluene, paraffins, tetrahydronaphthalene, alkylated naphthalenes; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; dimethylsulfoxide (DMSO); ketones, such as cyclohexanone; esters, such as lactate, carbonate, fatty acid ester, γ -butyrolactone; a fatty acid; a phosphonate ester; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, such as silicates, silica gel, talc, kaolin, limestone, lime, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium oxide; polysaccharides such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, such as cereal flour, bark flour, wood flour and nut shell flour, and mixtures thereof.
Suitable surfactants are surface-active substances, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof; such surfactants may be used as emulsifiers, dispersants, dissolution promoters, wetting agents, penetration enhancers, protective colloids or adjuvants.
Suitable adjuvants are compounds which have negligible or even no pesticidal activity per se and which improve the biological properties of the compounds I on the target; examples are surfactants, mineral or vegetable oils and other auxiliaries.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates, and the like.
Suitable anti-freeze agents are ethylene glycol, propylene glycol, urea, glycerol, and the like.
Suitable antifoams are polysiloxanes, long-chain alcohols and fatty acid salts, and the like.
Suitable colorants (e.g. colored in red, blue or green) are pigments and dyes of low water solubility, which may be inorganic colorants (e.g. iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin colorants, azo colorants and phthalocyanine colorants).
Suitable active substances which can be mixed with the active substances according to the invention in compounded or tank-mixed formulations are, for example, the substances known from the "national institute of New agricultural chemical technology" (national agricultural science and technology, publishers, 2010.9). For example, the fungicide active substances mentioned below may be mixed with the compounds of formula I (remarks: name of the compound, either by common name according to the International organization for standardization (ISO), or by chemical name, where appropriate with a code number): azoxystrobin (azoxystrobin), strobilurin (coumoxystrobin), coumoxystrobin (coumoxystrobin), dimoxystrobin (dimoxystrobin), enestroburin (enestrobin), fenaminostrobin (fenaminstrobin), fenoxystrobin/fluxastrobin (flufenoxystrobin), fluoxastrobin (fluoxystrobin), kresoxim-methyl (kresoxim-methyl), metominostrobin (metominostrobin), orysastrobin (orysastrobin), picoxystrobin (picoxystrobin), pyraclostrobin (pyraclostrobin), 2- [2- (2, 5-dimethylphenoxymethyl) phenyl ] -3-2- (2, 2-methoxyphenyloxymethyl) -3-methoxyacrylate, 2- (2-2, 5-N-methoxyiminoketoximin) -2- (2-methyl) -2- (2-methoxy-methyl) acetamide, 2- (2-methyl) phenyl) -2- (2-methyl) acetamide, 2-methyl-phenyl-2- (2-methoxy-methyl) acetamide, N-methyl-2-phenyl-2-methyl-phenyl-2-N-methoxyacetamide, N-methyl-2-methyl-one, N-methyl-phenyl-2-one, and N-one, Fenamidone (fenamidone); cyazofamid (cyazofamid), amisulbrom, [ (3S,6S,7R,8R) -8-benzyl-3- [ (3-acetoxy-4-methoxypyridine-2-carbonyl) amino ] -6-methyl-4, 9-dioxo-1, 5-dioxepin-7-yl ] 2-methylpropanoic acid [ (3S,6S,7R,8R) -8-benzyl-3- [ [ 3-acetoxymethoxy-4-methoxypyridine-2-carbonyl ] amino ] -6-methyl-4, 9-dioxo-1, 5-dioxepin-7-yl ] 2-methylpropanoic acid [ (3S,6S,7R,8R) -8-benzyl-3- [ (3-isobutoxycarbonyloxy-4-methoxypyridine-2-carbonyl) amino ] -6-methyl-4, 9-dioxo-1, 5-dioxepin-7-yl ] ester, 2-methylpropanoic acid [ (3S,6S,7R,8R) -8-benzyl-3- [ [3- (1, 3-benzodioxol-5-ylmethoxy) -4-methoxypyridine-2-carbonyl ] amino ] -6-methyl-4, 9-dioxo-1, 5-dioxepin-7-yl ] ester, 2-methylpropanoic acid (3S,6S,7R,8R) -3- [ [ (3-hydroxy-4-methoxy-2-pyridinyl) carbonyl ] amino ] -6-methyl-4, 9-dioxo-8- (phenylmethyl) -1, 5-dioxepin-7-yl ester; benoxanil, bixafen, boscalid (boscalid), carboxin (carboxin), furamex (fenfuram), fluopyram (flupyram), flutolanil (flutolanil), flutolanil (fluxapyroxad), furametpyr (furametpyr), isopyrazam, mepronil (mepronil), oxycarboxin (oxarboxin), penflufen, penthiopyrad (penthiopyrad), sedaxane, phylloquat (tecloftalam), fludioxonil (thifluzamide), N- (4' -trifluoromethylsulfanyl-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2- (1,3, 3-trimethylbutyl) phenyl) -1, 3-dimethyl-5-fluoro-1H-4-carboxamide, N- [9- (methylene) pyrazole-carbonyl ] -1-methyl-4-carboxamide, 2,3, 4-tetrahydro-1, 4-methylen-naphthalen-5-yl ] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; 3-difluoromethyl-1-methyl-N- (1,1, 3-trimethyl-2, 3-indan-4-yl) pyrazole-4-carboxamide, 3-trifluoromethyl-1-methyl-N- (1,1, 3-trimethyl-2, 3-indan-4-yl) pyrazole-4-carboxamide, 1, 3-dimethyl-N- (1,1, 3-trimethyl-2, 3-indan-4-yl) pyrazole-4-carboxamide, 3-trifluoromethyl-1, 5-dimethyl-N- (1,1, 3-trimethyl-2, 3-indan-4-yl) pyrazole-4-carboxamide, 3-difluoromethyl-1, 5-dimethyl-N- (1,1, 3-trimethyl-2, 3-indan-4-yl) pyrazole-4-carboxamide, 1,3, 5-trimethyl-N- (1,1, 3-trimethyl-2, 3-indan-4-yl) pyrazole-4-carboxamide; difluoroforest (diflumetorim), (5, 8-difluoroquinazolin-4-yl) - {2- [ 2-fluoro-4- (4-trifluoromethylpyridin-2-yloxy) phenyl ] ethyl } amine; nitrophenyl derivatives: binacryl, dinotefuran, dinocap, fluazinam; pyriminobac (ferimzone); an organometallic compound: triphenyltin-based salts, such as fentin-acetate, fentinchloride or fentinhydroxide; ametocradin and silthiopham (silthiofam); azaconazole (azaconazole), bitertanol (bitertanol), bromuconazole (broconazol), cyproconazole (cy, proconazole), difenoconazole (difenoconazole), diniconazole (diniconazole), diniconazole M (diniconazole-M), epoxiconazole (epoxyconazole), fenbuconazole (fenbuconazole), fluquinconazole (fluquinconazole), flusilazole (flusilazole), flutriafol (flutriafol), hexaconazole (hexaconazole), amidazole (imazoconazole), ipconazole (ipconazole), cyclopentconazole (metconazole), myclobutanil (epoxyconazole), oxyponazole, paclobutrazol (paclobutrazol), pyriconazole (bithiozole), pyriconazole (bitazone), pyriconazole (pyriconazole), pyriconazole (propiconazole), pyriconazole (propiconazole), pyriconazole (pyriconazole), pyriconazole (propiconazole), pyriconazole (pyriconazole), pyriconazole (propiconazole), pyriconazole (pyriconazole), pyriconazole (pyriconazole), pyriconazole (pyriconazole), pyriconazole (pyriconazole), pyriconazole (pyriconazole), pyriconazole (pyriconazole), pyriconazole (pyriconazole), pyriconazole (pyriconazole), pyridazole (pyriconazole), pyriconazole (pyriconazole), pyrimethazol (pyriconazole (pyrimethanil (pyriconazole), pyriconazole (pyridazole (pyriproxetil (pyrimethazol (pyriproxetil (pyrimethanil), pyriproxetil (pyrimethazol (pyriproxetil), pyrimethanil), pyrimethazol (pyriproxetil), pyrimethazol (pyriproxetil), pyriproxetil (pyrimethanil), pyri, Pyribenzoxim (pyrifenox), triforine (triforine), 4-dodecyl-2, 6-dimethylmorpholine (aldimorph), moroxydine (dodemorph), moroxydine-acetate (dodemorph-acetate), fenpropimorph (fenpropimorph), tridemorph (tridemorph), fenpropidin (fenpropidine), flutriafol (piperalin), spiroxamine (spiroxamine), benalaxyl (benalaxyl-M), kara-xyl (miraxyl-M), metalaxyl (metalaxyl), mefenoxamine (metalaxyl-M), flutolanilide (flutolanil), oxaziridine (fenoxam), flutolanilide (fenoxamine), fenhexamide (ofacial (fenoxanide), oxaziridine (fenpropidin), fenpyrad (fenpropidin), thizamide (fenpropiconazole), thiuracil (fenazamide), carbendazim (fenpropiconazole), carbendazid (carbendazim), carbendazim (fenzim), thiuracil (benazolin (benazolidone), thiuracil (benazol), thiuracil (benazolidone (benazol), thiuracil (benazol), benazol (benazolidone) (benazol), benazolidone) (benazol), benazolidone (benazolidone) (benazol), benazolidone) (benazol), benazolidone) (benazol), benazolidone (benazolidone) (benazol-methyl), benazolidone (benazolidone) (benazol), benazol-benazol), benazolidone (benazolidone) (benazol), benazolidone (benazolidone) (benazol), benazolidone (benazol), benazol-benazol), benazolone (benazol-methyl), benazol-methyl), benazol-benazolone (benazolone), benazolone (benazolidone (benazolone), benazolidone (benazolone, benazolidone (benazolone), benazol-benazolone (benazol), benazol-benazolone (benazolone), benazolone, Fluopicolide (fluopicolide), zoxamide (zoxamide), metrafenone (metrafenone), pyriofenone, cyprodinil (cyprodinin), mepanipyrim (mepanipyrim), pyrimethanil (pyrimethanil), blasticidin (bleticidin-S), kasugamycin (kasugamycin), kasugamycin hydrate (kasugamycin hydrate), milomycin (kasugamycin hydrate), streptomycin (streptomycin), oxytetracycline (oxytetracycline), polyoxin (polyoxine), validamycin (validamycin A), flunomycin (fluxoimimid), iprodione (iprodione), procymidone (vinclozolin), fenpiclonil (fenpropidium), fludioxonil (fluocinoxolone (fluopicolide), fenpyrazamide (fenpyrazofos), fenpyrazofos (fenpyrazofos), fenpyrazofen (fenpyrazofen-ethyl (fenpyrazofen), fenpyrazofenofos (fenpyrazofos), fenpyrazofos (fenpyrazofenofos (fenpyrazofos), fenpyrazofenofos (fenpyrazofenofos), fenpyrazofenofos (fenpyrazofos), fenpyrazofenofos (fenpyrazofenofos), fenpyrazofenoxasulfone (fenpyrazofenoxathion (fenpyrazofenoxasulfone), fenpyrazofenoxathion (fenpyrazofenoxathion), fenpyrazofenoxasulfone (fenpyrazofenoxathion), fenpyrazofenoxathion (fenpyrazofenoxathion), fenpyrazofenoxathion (fenpyrazofenoxathion), fenpyrazofenoxathion (fenpyrazofenoxathion), fenpyrazofenoxathion (fenpyrazofenoxathion), fenpyrazofenoxathion (fenpyrazofenoxathion), fenpyrazofenoxathion (fenpyrazofenoxathion), fenthion), fenpyrazofenoxathion (fenpyrazofenoxathion), fenpropithion (fenpyrazofenoxathion), fenpyrazofenoxathion (fenthio, Mandipropamid (mandipropamid), pyrimorph (pyrimorph), benthiavalicarb (benthiavalicarb), iprovalicarb (iprovalicarb), valifenalate, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) but-2-yl) carbamic acid 4-fluorophenyl ester, oryzanol (propamocarb), propamocarb-hydrochloride (propamocarb-hydroxychlorid), Bordeaux mixture (Bordeaux mixture), copper acetate, copper hydroxide, copper oxychloride (copperoxochloride), basic copper sulfate, ferbam (ferbam), mancozeb (mancozeb), maneb (maneb), metam (metam), metiram (metiram), methyl zineb (propineb), thiram (thiram), zineb (zineb), ziram (ziram), pyraflufen), fenpropineb (propineb), pyraflufen (chlorphenamid), dichloflufen (thion), captafalso (captan), captafalso (captafol), captafalso (captafolid), flufen (captan), flufen (captan), flufen (flufen), flufen, and the compound, flufen, and the compound, flufen, and the compound, flufen, and the compound, flufen, and the compound, flufen, and the compound, flufen, such as the compound, in the compound, and the compound, in, Hexachlorobenzene (hexachlorobenzene), pentachlorophenol (pentachlorophenol) and its salts, tetrachlorophthalide (phthalide), tolylfluanid (tolyfluoride), N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, dodecine free base, biguanide salt (guazatine), iminoctadine (guazatine-acetate), iminoctadine acetate (iminoctadine), iminoctadine triacetate (iminoctadine-triacetate), dioctadedine (iminoctadine-tris (acetylbenzoate)), dithianon (dithianon), 2, 6-dimethyl-1H, 5H- [1,4] dithiino [2,3-c:5,6-c' ] bipyrrolidine-1, 3,5,7(2H,6H) -tetralone, validamycin (polyoxin b), polyoxin (polyoxin b); a melanin synthesis inhibitor: pyroquilon (pyroquilon), tricyclazole (tricyclazole), chlorocyclopropylamide (carpropamid), dicloromethride (diclomet), fenpyrad (fenoxanil), acibenzolar-S-methyl, thiabendazole (probenazole), isotianil (isotianil), tiadinil (tiadinil), calcium prohexadione-calcium; phosphonic acid esters: phycophytate (foseyl), fosetyl-aluminum (foseyl-aluminum), phosphorous acid and its salts, bronopol (bronopol), ametrytis (chinomethionat), cyflufenamid (cyflufenamid), cymoxanil (cymoxanil), dazomet (dazomet), prochloraz (debarb), diclomezine (diclomezine), difenzoquat (difenzoquat), difenzoquat-methyl sulfate (difenzoquat-methyl sulfate), diphenylamine, fenpyrazamide (fenpyrazamine), flurbiprofen (fluetover), flusulfamide, flutianil, methiocarb (methasulfocarb), chlordine (nitropyrin), isopropyl-isoprox (nitropyrol), oxine-copper (oxine-copter), proquindoxe (prothioconazole), cumquat (flufenpyrad, flufenpyrazoxazide (flufenpyrad), trifloxystrobin (flufenpyrazone), etc.
Advantageous effects
In summary, due to the adoption of the technical scheme, the invention has the beneficial effects that:
the alkyl pyrimidinamine compound with the substituted pyrazole structure or the salt thereof which is acceptable as pesticide has excellent biological activity on wheat powdery mildew, satisfactory control activity on objects such as cucumber downy mildew and the like and excellent safety on crops.
Modes for carrying out the invention
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
By taking into account the economics, diversity and biological activity of the synthesized compounds, it is preferred that some of the compounds are listed in the following table. Specific compound structures are shown in table 1, and specific compound physical property data are shown in table 2. The compounds in tables 1-2 are only for better illustration of the invention and are not intended to be limiting, and those skilled in the art will not understand that the scope of the above subject matter of the invention is limited to the following compounds.
Figure BDA0003197889090000081
TABLE 1 Structure of Compounds of formula I
Figure BDA0003197889090000082
Figure BDA0003197889090000091
Figure BDA0003197889090000101
Figure BDA0003197889090000111
TABLE 21H NMR data
Figure BDA0003197889090000112
Figure BDA0003197889090000121
Figure BDA0003197889090000131
Methods for preparing the compounds of the present invention are illustrated in the following schemes and examples. The starting materials are commercially available or can be prepared by methods known in the literature or as shown in detail. It will be appreciated by those skilled in the art that other synthetic routes may also be utilized to synthesize the compounds of the present invention. Although specific starting materials and conditions for the synthetic routes are described below, they can be readily substituted with other similar starting materials and conditions, and variations or modifications of the preparation process of the present invention, such as various isomers of the compounds, are included in the scope of the present invention. In addition, the preparation methods described below may be further modified in accordance with the present disclosure using conventional chemical methods well known to those skilled in the art. For example, protecting the appropriate groups during the reaction, and the like.
Example 1
Synthesis of Compound I-1:
Figure BDA0003197889090000141
dissolving intermediate III-1(1.84g and 10mmol) in 40mL dichloromethane and placing the solution in a reaction bottle, adding intermediate II-1(2.57g and 10mmol) while stirring at room temperature, dropwise adding triethylamine (1.5eq), tracking the reaction by TLC (ethyl acetate: petroleum ether ═ 1:4, GF254, UV color development), removing the solvent after the reaction is completed, drying, separating and purifying by silica gel column chromatography to obtain compound I-1, 1.62g and white solid powder;1H NMR(500MHz,Chloroform-d)δ7.65–7.58(m,2H),7.30–7.27(m,2H),6.98(m,1H),4.19(t,J＝7.3Hz,2H),3.15(t,J＝7.4Hz,2H),2.66–2.62(m,2H),2.52–2.51(m,2H),2.50(s,3H),2.48(s,3H),1.47(m,2H),1.37(d,J＝7.4Hz,2H),0.90(t,J＝7.3Hz,3H).
example 2
Synthesis of Compound I-2:
Figure BDA0003197889090000142
dissolving the intermediate III-2(1.98g, 10mmol) in 40mL dichloromethane and placing the mixture in a reaction bottle, adding the intermediate II-2(2.57g, 10mmol) while stirring at room temperature, dropwise adding triethylamine (1.5eq), tracking the reaction by TLC (ethyl acetate: petroleum ether ═ 1:4, GF254, UV color development), removing the solvent after the reaction is completed, drying, separating and purifying by silica gel column chromatography to obtain compound I-2, 2.10g, white solid powder;1H NMR(500MHz,Chloroform-d)δ7.66–7.57(m,2H),7.30–7.28(m,2H),6.99(m,1H),4.19(t,J＝7.3Hz,2H),3.17(t,J＝7.4Hz,2H),2.73–2.69(m,2H),2.65–2.62(m,2H),2.52–2.49(m,2H),2.49(s,3H),1.47(m,2H),1.38(d,J＝7.4Hz,2H),1.18(d,J＝7.0Hz,3H),0.90(t,J＝7.3Hz,3H).
example 3
Synthesis of Compound I-3:
Figure BDA0003197889090000151
dissolving the intermediate III-3(2.12g and 10mmol) in 40mL of dichloromethane, placing the dichloromethane in a reaction bottle, adding II-3(2.57g and 10mmol) while stirring at room temperature, dropwise adding triethylamine (1.5eq), tracking the reaction by TLC (ethyl acetate: petroleum ether: 1:4, GF254, UV color development), removing the solvent after the reaction is completed, drying, separating and purifying by silica gel column chromatography to obtain the target compound I-3, 2.43g and white solid powder;1H NMR(500MHz,Chloroform-d)δ7.65–7.58(m,2H),7.31–7.28(m,2H),6.98(m,1H),4.18(t,J＝7.3Hz,2H),3.57(m,1H),3.15(t,J＝7.4Hz,2H),2.65–2.62(m,2H),2.53–2.48(m,2H),2.48(s,3H),1.47(m,2H),1.37(d,J＝7.4Hz,2H),1.35–1.33(m,6H),0.90(t,J＝7.3Hz,3H).
example 4
Synthesis of Compound I-79:
Figure BDA0003197889090000152
dissolving the intermediate III-79(1.98g and 10mmol) in 40mL of dichloromethane, placing the dichloromethane in a reaction bottle, adding II-79(2.57g and 10mmol) while stirring at room temperature, dropwise adding triethylamine (1.5eq), tracking the reaction by TLC (ethyl acetate: petroleum ether: 1:4, GF254 and UV color development), removing the solvent after the reaction is completed, drying, separating and purifying by silica gel column chromatography to obtain the target compound I-79, 2.22g and white solid powder;1H NMR(500MHz,Chloroform-d)δ7.62–7.59(m,2H),7.30–7.27(m,2H),6.99(m,1H),4.13(m,2H),3.11(t,J＝6.4Hz,2H),2.52(s,3H),2.48(s,3H),2.09–2.05(m,2H),1.89(m,2H),1.49–1.45(m,2H),1.39–1.36(m,2H),1.28(d,J＝5.9Hz,2H),0.92(t,J＝7.3Hz,3H).
example 5
Synthesis of Compound I-80:
Figure BDA0003197889090000153
dissolving the intermediate III-80(2.12g and 10mmol) in 40mL of dichloromethane, placing the dichloromethane in a reaction bottle, adding II-80(2.57g and 10mmol) while stirring at room temperature, dropwise adding triethylamine (1.5eq), tracking the reaction by TLC (ethyl acetate: petroleum ether: 1:4, GF254 and UV color development), removing the solvent after the reaction is completed, drying, and separating and purifying by silica gel column chromatography to obtain the target compound I-80, 2.56g and white solid powder;1H NMR(500MHz,Chloroform-d)δ7.63–7.59(m,2H),7.31–7.28(m,2H),6.98(m,1H),4.14(m,2H),3.11(t,J＝6.4Hz,2H),2.74–2.70(m,2H),2.48(s,3H),2.08–2.05(m,2H),1.89(m,2H),1.49–1.47(m,2H),1.39–1.36(m,2H),1.29(d,J＝5.9Hz,2H),1.18(d,J＝7.0Hz,3H),0.91(t,J＝7.3Hz,3H).
example 6
Synthesis of Compound I-81:
Figure BDA0003197889090000161
dissolving the intermediate III-81(2.26g and 10mmol) in 40mL of dichloromethane, placing the dichloromethane in a reaction bottle, adding II-81(2.57g and 10mmol) while stirring at room temperature, dropwise adding triethylamine (1.5eq), tracking the reaction by TLC (ethyl acetate: petroleum ether: 1:4, GF254 and UV color development), removing the solvent after the reaction is completed, drying, separating and purifying by silica gel column chromatography to obtain the target compound I-81, 2.86g and white solid powder;1H NMR(500MHz,Chloroform-d)δ7.63–7.59(m,2H),7.31–7.28(m,2H),6.98(m,1H),4.14(m,2H),3.75(m,1H),3.11(t,J＝6.4Hz,2H),2.48(s,3H),2.08–2.05(m,2H),1.89(m,2H),1.49–1.47(m,2H),1.39–1.36(m,2H),1.35–1.33(m,6H),1.29(d,J＝5.9Hz,2H),0.91(t,J＝7.3Hz,3H).
example 7
Preparation of the preparation:
1. wettable powder: weighing 30% of the compound of formula (I), 4% of calcium lignosulfonate, 2% of sodium lauryl sulfate, 3% of white carbon black and kaolin to 100%. Mixing uniformly, and obtaining the product after air current crushing.
2. Water dispersible granules: 50% of the compound of formula (I), 6% of sodium lignosulfonate, 10% of sodium naphthalenesulfonate formaldehyde condensate, 2% of polyvinylpyrrolidone, 3% of sodium laurylsulfate, 5% of carboxymethylcellulose and kaolin are weighed up to 100%. Uniformly mixing, after airflow crushing, weighing the powder, adding water for mixing, granulating in a granulator, and then drying and screening to obtain granular products.
The above are all weight percentages.
Example 8
Wheat powdery mildew protective control test (Erysiphe graminis):
the host crop is wheat (Roughwheat 7), and the specific operation is as follows:
weighing a certain mass of compound sample, dissolving in acetone, and preparing into mother liquor for later use. In the test, compound samples and control agents were prepared into serial concentration gradient solutions with 0.1% tween 80 in water for in vivo screening. And selecting wheat seedlings with consistent growth vigor in the 2-3 leaf stage, and placing the wheat seedlings in sequence for later use after marking. The sprayer is a spray tower, 30mL of liquid medicine is sprayed for each treatment, and the liquid medicine is naturally dried. After 24h, inoculating pathogenic bacteria, and setting blank control and other medicament control. Uniformly shaking off and inoculating powdery mildew fresh spores generated in 24 hours on ill wheat leaves onto treated potted wheat seedlings in 2-3 leaf periods, bagging the inoculated wheat seedlings by using a black plastic bag, preserving moisture for 12 hours, and adjusting the humidity in a greenhouse to 50% for normal culture. After 7-10 days, the disease is completely developed by clear water contrast, and the test result is investigated. And carrying out grading investigation according to the disease condition of blank control after culturing for 5-7 d under the appropriate condition.
A: the control effect is more than 90 percent;
b: the control effect is more than 80 percent;
c: the control effect is between 50 and 79 percent;
d: the control effect is less than 50 percent.
Control 1:
Figure BDA0003197889090000171
control 2:
Figure BDA0003197889090000172
the results of the wheat powdery mildew protective test are shown in table 3.
TABLE 3 wheat powdery mildew protective test results
Figure BDA0003197889090000173
Example 9
Cucumber downy mildew protective control test (Pseudoperonospora cubensis):
the host crop is cucumber (Taian Mici), and the method adopts a potted seedling method, and comprises the following specific operations:
weighing a certain mass of compound sample, dissolving in acetone, and preparing into mother liquor for later use. In the test, compound samples and control agents are prepared into serial concentration gradient liquid medicines by using 0.1 percent of Tween 80 in water and used for screening living bodies. And selecting potted cucumber seedlings with 4-6 leaf stages which grow regularly and consistently as test host plants of the cucumber downy mildew. The sprayer is a spray tower, 30mL of liquid medicine is sprayed for each treatment, and the liquid medicine is naturally dried. After 24h, the pathogens are inoculated, and blank control and other medicament control are set. The downy mildew spores on the leaves of the cucumber with disease are prepared into suspension (the concentration is 1 multiplied by 10)5spores/mL), sprayed onto inoculated leaves, and cultured under appropriate conditions. After 7-10 days, the disease is completely developed by clear water contrast, and the test result is investigated.
The control effect grade is as follows:
a: the control effect is more than 90 percent;
b: the control effect is more than 80 percent;
c: the control effect is between 50 and 79 percent;
d: the control effect is less than 50 percent.
Control 1:
Figure BDA0003197889090000181
control 2:
Figure BDA0003197889090000182
the results of the cucumber downy mildew resistance test are shown in Table 4.
TABLE 4 cucumber downy mildew protection test results
Figure BDA0003197889090000183
Figure BDA0003197889090000191
The above embodiments are only for illustrating the technical concept and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention accordingly, and not to limit the protection scope of the present invention accordingly. All equivalent changes or modifications made in accordance with the spirit of the present disclosure are intended to be covered by the scope of the present disclosure.

Claims (12)

1. A substituted pyrimidinamine compound or a pesticidally acceptable salt thereof, having the formula:
Figure FDA0003597422190000011
in the formula (I), the compound is shown in the specification,
R1selected from H, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6Alkoxy, n is an integer selected from 0 to 5;
R2is selected from H or C1-C6An alkyl group;
R3selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or C3-C6A cycloalkyl group;
R4selected from hydrogen, halogen, C1-C8Alkyl, halo C1-C8Alkyl radical, C1-C8Alkoxy or C3-C8A cycloalkyl group;
R5selected from H, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
R6selected from H, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
or, R5And R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 8;
R7selected from H, halogen, CN, nitryl, aldehyde group, carboxyl, hydroxyl and C1-C4Alkyl, halo C1-C4Alkyl radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl, unsubstituted phenyl or substituted by C1-C4Alkyl-substituted phenyl.
2. A substituted pyrimidinamine compound or a pesticidally acceptable salt thereof according to claim 1, wherein in formula (I), R is1Selected from H, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4Alkoxy, n is an integer selected from 0 to 5;
R2is selected from H or C1-C4An alkyl group;
R3selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or C3-C6A cycloalkyl group;
R4selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or C3-C6A cycloalkyl group;
R5selected from H, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R6selected from H, C1-C6Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
or, R5And R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 7.
3. A substituted pyrimidinamine compound or a pesticidally acceptable salt thereof according to claim 2, wherein in formula (I), R5And R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 6.
4. A substituted pyrimidinamine compound or a pesticidally acceptable salt thereof according to claim 1, wherein in formula (I), R is1、R2Each independently selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt, CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3、CH2CF3、CH2CH2Cl, vinyl or cyclopropyl;
R3、R4each independently selected from H, F, Cl, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt or cyclopropane;
R5and R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 5;
R7selected from H, F, Cl, Br, CN, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3、CH2CF3、CH2CH2Cl, vinyl, OMe, OEt, n-PrO, i-PrO, n-BuO, i-BuO, s-BuO, t-BuO, cyclopropane, nitro, aldehyde group, carboxyl and hydroxyl.
5. A substituted pyrimidinamine compound or a pesticidally acceptable salt thereof according to claim 4, wherein in formula (I), R1、R2Each independently selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt or cyclopropane;
R3、R4each independently selected from H, F, Cl, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt or cyclopropane;
R5and R6Together form a radical- (CH)2)t-, t represents an integer of 2 to 5;
R7selected from H, F, Cl, Br, CN, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3Vinyl, OMe, OEt, n-PrO, i-PrO, n-BuO, i-BuO, s-BuO, t-BuO, cyclopropane, nitro, aldehyde group, carboxyl group and hydroxyl group.
6. A substituted pyrimidinamine compound or a pesticidally acceptable salt thereof according to claim 5, wherein in formula (I), R1、R2Are all H, and n is 5;
R3selected from H, Me or Et;
R4is n-Bu;
R5and R6Together form a radical- (CH)2)t-, t represents 3 or 4;
R7selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, cyclopropane.
7. A substituted pyrimidinamine compound or a pesticidally acceptable salt thereof according to any of claims 1 to 6, selected from the group consisting of:
Figure FDA0003597422190000021
Figure FDA0003597422190000031
8. a fungicidal composition comprising at least one of the substituted pyrimidinamine compounds according to any of claims 1 to 7 or as a pesticidally acceptable salt thereof in a fungicidally effective amount.
9. The bactericidal composition of claim 8, further comprising a formulation carrier or formulation auxiliary.
10. A method for controlling plant diseases, which comprises applying a biologically effective amount of at least one of the substituted pyrimidinamine compounds or the salts thereof as pesticidally acceptable according to any one of claims 1 to 7 or the fungicidal composition according to claim 8 to plants.
11. Use of at least one of the substituted pyrimidinamine compounds or the salts thereof as a pesticidal agent according to any of claims 1 to 7 or the fungicidal composition according to any of claims 8 to 9 for controlling plant diseases.
12. The use according to claim 11, wherein the plant disease is a viral disease, a bacterial disease or a fungal disease.
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